Pineland Vacations from $407

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Your Pineland Vacation

Say bye-bye to the worries of planning and hello to a Pineland vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with North Captiva, which is good for watersports, cycling and coastal beaches. Ready to venture out and explore? Calusa Heritage Trail, Randell Research Center and Useppa Museum are just three of the best places to visit during your trip to Pineland. No matter your travel plans or the size of your budget, putting together a tailored Pineland vacation is a piece of cake with Expedia.

The Latest Pineland vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Save 100% on your flight
Price was $743, price is now $407 per person
$407
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,612 reviews)
Third time here. Live it! Will come back soon.

Reviewed on Nov 26, 2025

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Price was $1,540, price is now $791 per person
$791
per person
Jan 14 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.8/10 Exceptional! (1,027 reviews)
We absolutely loved our stay at Fisherman's Village! The night time front desk person was so friendly and helpful....top notch! There are easily accessible walking and bike trails going directly from the property. We rented E bikes from Jersey Joe's and were able to zip around the city and visit all sorts of great restaurants and venues. Our room was cozy and spotless. We would definitely stay here again.

Reviewed on Nov 24, 2025

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

4 out of 5
Downtown Punta Gorda
Save 100% on your flight
Price was $989, price is now $603 per person
$603
per person
Jan 14 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9/10 Wonderful! (1,003 reviews)
Pleasant staff. Great art. Well appointed room.

Reviewed on Nov 24, 2025

Tropical-waterfront - Heated Pool-spa-dock-kayaks-bikes

Tropical-waterfront - Heated Pool-spa-dock-kayaks-bikes

2 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $5,802, price is now $4,369 per person
$4,369
per person
Feb 4 - Feb 11
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Punta Gorda Airport (PGD)
No reviews
Hibiscus Heated Pool Private Dock Bikes Kayaks Walk to Fishermen s Village

Hibiscus Heated Pool Private Dock Bikes Kayaks Walk to Fishermen s Village

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $4,757, price is now $3,708 per person
$3,708
per person
Feb 4 - Feb 11
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Punta Gorda Airport (PGD)
No reviews
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Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
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Discover the most popular places to visit in Pineland

Koucky Gardens & Gallery

You can spend time exploring the galleries in Koucky Gardens & Gallery in Pine Island Center. Wander the beautiful beaches and marina in this family-friendly area.

Koucky Gardens & Gallery

Goodwins Island

Commune with nature and explore the great outdoors at Goodwins Island during your travels in Bokeelia. Take in the museums while you're in the area.

Goodwins Island

Useppa Museum

You can spend time studying the exhibits at Useppa Museum in Bokeelia. Amble around the area's marina, or seek out its fishing spots.

Useppa Museum

What to do in Pineland

Close-up encounters with our beautiful Dolphins

Private Dolphin & Sightseeing Boat Day Tour

$185
per adult
Private Dolphin & Sightseeing Boat Day Tour
See all activities in Pineland

Pineland Hotel Deals

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
$204 nightly
The price is $228 total per night from Dec 17 to Dec 18
$228 total
Dec 17 - Dec 18
Total with taxes and fees
8.8/10 Excellent! (1,655 reviews)
This is a wonderful hotel, rooms are beautiful and amenities wonderful. We will definitely come back.

Reviewed on Nov 23, 2025

Margaritaville Beach Resort Fort Myers
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $182 total per night from Nov 30 to Dec 1
$182 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,038 reviews)
Everything was perfect.

Reviewed on Nov 28, 2025

Lani Kai Beachfront Resort
Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

2.5 out of 5
4850 S Cleveland Ave Fort Myers FL
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $68 total per night from Nov 30 to Dec 1
$68 total
Nov 30 - Dec 1
Total with taxes and fees
6.6/10 (1,010 reviews)
The parking lot needed more lighting at night. Room was average, I was just passing through town for the night and it served its purpose.

Reviewed on Nov 21, 2025

Baymont by Wyndham Fort Myers Central
See all 13,307 properties in Pineland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Pineland Vacation Packages

Pineland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Southwest Florida Intl. Airport (RSW)
Top Sights
Museum of the Islands, Useppa Museum and Calusa Heritage Trail

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Frequently asked questions

How much does a Pineland vacation package cost?
You can grab a vacation package to this popular destination from $407 on Expedia. However, how much your vacation to Pineland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Pineland?
If you'd like to score a cheap Pineland vacation package, consider planning a trip in September, October and December. You'll typically find lower rates on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Pineland?
The ideal length for your Pineland vacation depends on what you'd like to do. Usually, a few days to a week will give you time to visit all the leading sights and discover some hidden treasures along the way.
How to find the best Pineland package deals?
Use Expedia's filter tool to help you find some terrific Pineland package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Pineland package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Pineland vacation as a package?
You can enjoy significant savings on your Pineland escape by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Pineland?
If you have your Pineland travel dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Pineland?

  1. Choose when to go: Check your schedule and get packing. Your favorite time of year and the activities on offer will also help you decide when to escape to Pineland.
  2. Figure out your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and experiences. Your accommodations will probably be the largest expense during your trip to Pineland.
  3. Explore Pineland with our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Pineland. You can also save your must-visit places, collaborate with friends and family and organize all your plans in one place.
  4. Determine how many days away: Start by compiling a list of the attractions and activities you want to get to in Pineland. Then, estimate how long you'll need at each, along with any travel time.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Pineland vacation package that brings all your bookings together.
  6. Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Check out some of the exciting things to do in Pineland in Pineland and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Pineland vacation packages?
Secure your ideal getaway to Pineland with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.